title: A colorimetric chiral sensor based on chiral crown ether for the recognition of the two enantiomers of primary amino alcohols and amines.
abstract: A new colorimetric chiral sensor material consisting of three different functional sites such as chromophore (2,4-dinitrophenylazophenol dye), binding site (crown ether), and chiral barrier (3,3'-diphenyl-1,1'-binaphthyl group) was prepared and applied to the recognition of the two enantiomers of primary amino alcohols and amines. Among five primary amino alcohols and two primary amines tested, the two enantiomers of phenylalaninol show the highest difference in the absorption maximum wavelength (Δλ(max)=43.5 nm) and in the association constants (K(S)/K(R)=2.51) upon complexation with the colorimetric chiral sensor material and, consequently, the two enantiomers of phenylalaninol were clearly distinguished from each other by the color difference.
authors.affiliation: Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea.
authors.forename: Eun Na Rae
authors.initials: EN
authors.lastname: Cho
authors.forename: Yinan
authors.initials: Y
authors.lastname: Li
authors.forename: Hee Jin
authors.initials: HJ
authors.lastname: Kim
authors.forename: Myung Ho
authors.initials: MH
authors.lastname: Hyun
mesh_terms: D000588:Amines / Q000032:analysis / Q000737:chemistry*; D000605:Amino Alcohols / Q000032:analysis / Q000737:chemistry*; D002853:Chromatography, Liquid / Q000379:methods; D003124:Colorimetry / Q000379:methods*; D043844:Crown Ethers / Q000737:chemistry*; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry; D007189:Indans / Q000032:analysis / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry; D009281:Naphthalenes / Q000737:chemistry; D010456:Peptides, Cyclic / Q000737:chemistry*; D010627:Phenethylamines / Q000032:analysis / Q000737:chemistry; D010649:Phenylalanine / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry; D011412:Propanolamines / Q000032:analysis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C530035:(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6; D000588:Amines; D000605:Amino Alcohols; D043844:Crown Ethers; D004983:Ethanolamines; D007189:Indans; D009281:Naphthalenes; D010456:Peptides, Cyclic; D010627:Phenethylamines; D011412:Propanolamines; C110394:chemosensor 1; C110395:chemosensor 2; C012481:phenylalaninol; C016992:1-aminoindan; D010649:Phenylalanine; C005332:N-phenylethanolamine; C417575:leucinol; C034448:2-aminopropanol; D007930:Leucine; D005998:Glycine; C008544:monoisopropanolamine